2-Fluoroethyl bromide → HCID 86606184, compound

HRID 2112095Notes

Reaction equation

HRID 2112095 reaction equation
[CH2:1]([N:8]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[C:17](=[O:19])[NH:16][CH2:15][CH2:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:28][CH2:29][F:30].[H-].[Na+]>C(OCC)(=O)C>[CH2:20]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[C:17](=[O:19])[N:16]([CH2:28][CH2:29][F:30])[CH2:15][CH2:14]2)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 129822-Fluoroethyl bromideHCID 24758Sodium hydrideHCID 67095279HCID 67095279, compound

Product 1

HCID 86606184HCID 86606184, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1.06 g (3.095 mmol) 8-dibenzylamino-3,4-dihydro-2H-isoquinolin-1-one are combined with 1.5 ml (12 mmol) 1-bromo-2-fluoro-ethane and at ambient temperature 780 mg (19.50 mmol) sodium hydride are added batchwise over a period of 30 h. The reaction mixture is diluted with ethyl acetate and extracted with sodium hydrogen carbonate solution. The organic phases are dried and the solvent is eliminated in vacuo. The crude product is purified by column chromatography. The carrier used is silica gel and the eluant used is dichloromethane, to which 5% of a mixture of 90% methanol and 10% saturated aqueous ammonia solution have been added.

Workup

  1. additionare added batchwise over a period of 30 h
  2. extractionextracted with sodium hydrogen carbonate solution
  3. customThe organic phases are dried
  4. customThe crude product is purified by column chromatography
  5. additionto which 5% of a mixture of 90% methanol and 10% saturated aqueous ammonia solution have been added

Sources & evidence

ORD record
ord-3dc136404b59405398c72f3acbd7fe82
Source dataset
uspto-grants-2009_04
Patent number
US07521457B2

Reaction notes

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